


Something About Exploring

by Zoozleplug (Josie_Lynn)



Category: Game Grumps, jacksepticeye
Genre: Genderplay, Impact Play, Multi, god this is the first time i tried to write this stuff, so if it's bad im sorry
Language: English
Status: Completed
Published: 2018-04-01
Updated: 2018-04-01
Packaged: 2019-04-16 16:23:10
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,657
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14168826
Author URL: https://archiveofourown.org/users/Josie_Lynn/pseuds/Zoozleplug
Summary: Sometimes plans falls through, but that's okay, because your girlfriend is always coming up with newer, better ones.





	Something About Exploring

“You want me to do what?” Dan’s spoon dropped into his cereal as he sat around Jack and Holly, who had been giving him expectant looks.

“We want to experiment with dips and we'll need your help with it.” Holly repeated, the expectant look fading from her features. Jack's face was flushed now, staring down into his own bowl.

“No, yeah, I heard that, but my question is-” Dan paused, closing his eyes and tapping at his temple. He was trying to find the right words to express his emotions. “What exactly are…. 'dips’?” Jack lifted his head, eyes peering over at Holly as he awaited her response.

“Well….” Holly began, twisting her hands together, “They're….uh…”

“It's what some people call adult diapers.” Jack finished.

“Oh..” Dan said quietly, “Oh! That's….okay?”

“The concept or our proposal?” Holly asked.

“The concept is, but like….do people _really_ do that?”

“Oh, most definitely.” Jack interjected, “There’s a whole community and everything. You know it’s legit if they’ve got a community.”

“A lot of shitty things have communities, but alright then.” Dan frowned.

“Dan, if you don’t want to do this with us, it’s fine.”

“It’s not that!” Dan said too loudly. He took a deep breath, “I just… I don’t know exactly what you want me to do.” He shrugs with a frown, looking down at his cereal. He begins to play with it, just enough to try and get his attention enough that the heat fades off his face.

“I guess it’s just….helping us pick out stuff and putting them on?”

“...You want me to buy you stuff and change you?” Dan asked. They both nodded, and now Jack was looking back down into his cereal.

“When you put it like that, you make it sound like it’s a bad thing.” Jack laughed nervously and Dan quickly held onto his hand that rested on the table.

“It’s not! I’m having trouble wrapping my head around it, that’s all.”

“We’re not trying to put you in anything, Dan,” Holly reassured him, “We are just asking your permission. You don’t have to say yes.”

Dan looked between the two. Jack was peeking up at him and Holly’s hands were under the table, but Dan could tell she was obviously fidgeting.

“I’m down for it.” Dan felt the tension dissipate in the room as Jack lifted his head and Holly’s shoulders dropped. Jack’s hand turned around, squeezing lightly on Dan’s palm, a nervous smile on both of their faces.

“Cool. There’s a place we can go to to pick cool stuff out.” Holly said as she picked up her previously finished bowl and headed to the sink.

“What, like a CVS or something?” Dan said as he continued to eat his cereal.

“Eww, gross. You don’t want to get diapers from there, they’re all boring.” She tossed her bowl in and started running the warm water. Briefly the older man wondered what she meant by ‘boring’, his eyebrows knitting together. Weren’t all diapers the same? He remembers coming across cartoon diapers with cars and Disney Princesses on them once when he was getting toilet paper, but would they sell those in adult sizes? Hmm.

“Rite-Aid?” Dan guesses.

“It’s not a drugstore,” she said, “it’s a place Ross and I frequent. They’re pretty underground, but they sell a bunch of kink stuff.”

“You and Ross do this?” Holly shook her head.

“We thought about it, but Ross isn’t exactly the…’Daddy’ type, if that makes sense.”

“The what?” Dan was getting confused. He knew the basic terms, but there was still stuff he was unfamiliar with. Well, he’d most certainly heard of the Daddy kink thanks to the comments on his Instagram, but he was pretty sure that they were two different things. Pretty sure, almost positive. Maybe.

“We’ll explain everything to you on the ride there, right Jack?” Holly called out to him from the hallway. Jack raised his thumb up in approval as he stood up from his place at the table, grabbing his own bowl as he released Dan’s hand with a soft pat.

“It’s gonna be fuuuun.” The younger man danced to the sink, and Dan placed his fist underneath his chin as he thought about how the day would go. He was sure he wasn’t prepared, but he trusted them. They would take care of him, and he would most certainly take care of them.

* * *

 

The store Holly had talked about wasn’t much of a store at all. Dan would describe it as more of a classy warehouse, sectioned off for the multiple kinks it held. Almost like Costco, but way more interesting and not as crowded. There was a wall that held leashes and collars, another held whips and riding crops. Dan was in awe by it all until he felt Jack’s hand pulling him forward and to a shelf stacked high with...mysterious boxes.

Holly was pointing up at the top row, speaking to a woman with too many piercings in Dan’s opinion.

“So you and Ross finally decided to try your hands at some diapered Little stuff?” The woman said as Dan got closer. Holly laughed and turned, catching sight of Dan and smiling wider.

“No, actually. Ross is still too much of a brat to buckle down and really do anything. So Dan,” Holly placed her hand on his forearm, “Is gonna be taking his place instead.” The woman turned to him and pursed her lips.

“You’re new to this, aren’t you?” She asked. Dan’s pride almost got the best of him as he began to shake his head no. “Mmm. Alright then.”

“He’s new to...this side of it all.” Jack spoke up from beside him. The woman nodded and turned her back to them, opening her arms up to the wall. “We got him though, so don’t worry.”

“Well, these are just our available packages. They come in all kinds of different designs and sizes. Just give me a shout if you need my help, okay?” Holly gave a thumbs up as the woman walked away, leaving Dan alone with the two.

“How are you feeling so far about this?” Holly asked, taking Dan’s free hand and squeezing it.

“Is ‘confused’ a proper emotion? Because I’m it.” Dan said, looking up at the shelves. Holly laughed.

“Well that’s a valid emotion,” She let go of his hand and stepped closer to the wall,  pointing to a box. “This one. It’ll be good for you, Jack.” Jack nodded in agreement.

“You think so?”

“Hell yeah,” Dan watched them closely.

He didn’t quite understand what was being talked about. Of course he knew what were inside these boxes, he wasn’t stupid. But it still felt surreal to be here, to be considering this. Of course he wouldn’t be the one they’d be putting in… God, it even felt weird to think of it. It wasn’t a taboo word. Diaper. Diaper, diaper, diaper. It was a normal word, but something felt wrong when he thought about it in this context.

“Alright,” Jack tapped Dan’s shoulder, “We’re ready to go.”

“Got what you need?” Holly, holding a box in her arms, nodded with a reassuring smile.

“Yup. Let’s pay for this and get going.”

He shouldn’t be this nervous, it was just like any other kink after all.

Even if he wasn’t being honest with himself, he’d push that aside and do this for Jack and Holly. This was important to them.

 

“So, you just put them on?” Dan watched as Jack and Holly poked through the box they’d bought.

“Yeah, but we’d need your help with caring for us, ya know?” Jack explained as if it were a simple thing everyone did. Dan knew better than to thinking that everyone was familiar with relationships and dynamics like this.

“God, this is weird,” Dan mumbled under his breath. He hadn’t been trying to judge the dynamic, at least not out loud. He considered himself to be an open-minded person about everything, even the stuff that admittedly weirded him out to the core. But this wasn’t sitting well with him.

He didn’t know why.

“This one has little ducks on it,” Holly commented, focused entirely on the contents of the box. Jack, however, was focused on Dan. He had a worried look, as if he had heard Dan's mumbles. He nodded his head towards the door, giving the silent sign that he wanted to talk to the other man. Nervously Dan stood up from his crouching position, frowning slightly with anxiety pooling in his belly.

Following Jack out of the room, Dan stuffed one of his hands into his pocket, the anxiety  for the upcoming conversation spiking.

“What’s up, dude?” Jack leaned against the wall, “You seem tense about this situation.”

“Me? Nah,” Dan lied, “Just so…” He trails off quietly, debating his next words, “stoked.”

“You’re weirded out.”

“Of course I’m not,” Jack gave him a look. “Okay, maybe I’m a little bit weirded out.” He admits carefully, the hand in his pocket coming out to nervously tug at his shirt.

“No, really?” Jack joked. The older man laughed, embarrassed. “Look, if this makes you uncomfortable, we can do something else.”

Dan let out a deep sigh, palming his face. He didn’t want to let his partners down, after all they had gotten this far, bought the diapers and everything. But Dan also knew it wasn’t a good idea to try something he didn’t fully agree with, that was just stupid. Maybe eventually, Dan thinks, but right now? ...He just doesn’t know.

“...Alright.” Jack grabbed Dan’s wrist and pulled it away from his face. “What do I do now?”

“You do the obvious,” Jack pulled Dan back into the room and leaned into his ear, “tell Holly what you tried to tell me.”

“But what if she’s hurt by it?” Dan frowned. Sure, Jack was able to take it well because he’s Jack, but Dan didn’t know what he’d do if he upset Holly with it. Hell, she’d been the one to bring it up and had looked the happiest when he agreed to it. What if this crushed her?

“I promise you she won’t be.” Jack whispered, patting Dan on the back as he pushed him to Holly. Dan bumped into her, causing her to jump slightly. She turned and sighed, a sigh of relief supposedly.

“Dan, Jack, I almost didn’t notice you guys left,” she laughed, “where’d you guys go?”

“To talk,” Jack said, nodding his head at Dan, “right, Dan?”

“Yeah,” Dan said blankly before perking up, “yeah! Holly, can we talk for a moment about,” he motioned to the box, “all this?”

“Oh,” Holly sat on the bed quickly, “what’s up?”

“Holly, I love you, but,” Dan scratched the back of his neck, “I don’t think I can do...this.”

“The relationship?” Holly’s voice quavered for a second, and Dan quickly sunk to his knees and grabbed her hands.

“No, no, not that,” he reassured her, “I mean, this kink.”

“Oh,” Holly breathed in relief, “well. That’s alright.” She smiled.

“Really?” Dan was surprised.

“Yeah,” she patted his head, “I’m not gonna push this on you if you aren’t down with it.”

“Oh thank god.” Dan released an audible sigh of relief, his shoulders relaxing as his head tipped back.

“What, you’d think I’d be angry at you or something?”

“Yeah!” Dan said worriedly, his head coming back up to look at her. “I was going crazy because you seemed so excited about doing this and I didn’t want to let you down.”

“You wouldn’t be letting me down, you idiot,” Holly giggled, “it’s just a kink we wanted to explore with you. There are things we explored that we haven’t liked, why did you think this would be any different?”

“I-” Dan thought for a moment, “I don’t know.” She had a point. They’d tried a lot of questionable things, things that put them in worse positions than what Holly and Jack had suggested. Dan’s discomfort with this was probably what made confessing harder, but he wouldn’t tell her that.

“Dan, it’s alright if you don’t want to do everything that we’re into,” Jack squeezed his shoulder, “we don’t need you to be one hundred percent down with everything.”

“But-” Dan began before Holly kissed his cheek.

“But nothing,” Holly offered, “We love you, and you deserve to feel as comfortable in this relationship as we do.”

Dan opened his mouth to speak, but all that came out was a dry laugh.

“Now that the sappy shit’s outta the way,” Jack waved his hand, “We should probably set up something else for us to do.”

“I have an idea.” Holly said.

“You do?” Jack raised an eyebrow.

“Yeah,” She stood up and walked to the dresser, opening the bottom drawer and searching, “but first: how do you guys feel about wearing skirts?”

“What?” Jack and Dan asked together.

* * *

Jack and Dan stood in front of Holly, shuffling around in their skirts as she watched them intensely. She was dressed in slacks and a loosely fitting dress shirt, the buttons undone at the collar. She looked good. No, she looked fucking  _ amazing _ . The bulge in her pants, hinting that she’d strapped up before getting dressed, just added to the look. She was leaning against the wall and she bit her lip momentarily until she began to speak.

“Well, hello,  _ girls _ ,” Holly said teasingly, “aren’t you looking lovely today.”

“Thank you, sir,” Jack said in a high voice. Dan snorted beside him and Holly put her hand over her mouth to cover her own giggles.

“I’m sorry,” Dan said, his laughing becoming more evident, “Your girl voice is just really fucking bad, dude.”

“Oh, like yours is any better,” Jack retorted, chuckling.

“Guys, guys,” Holly laughed, “Let’s just get back to the scene, please?”

Dan and Jack nodded, placing their hands back on the hems of their skirts. Holly’s eyes narrowed once more as she fell back into her role.

“You’re looking very nice as well, sir,” Dan said, choosing to be the confident one in the scene. Jack nodded along, looking between the two.

“You think so?” Holly smirked, sliding her own hand up her neck.

“Yeah, very  _ sexy _ .” Dan twirled his hair around his fingers and leaned forward, smiling.

“Sexy, huh?” Holly smiled.

Jack watched silently as the two flirted. Dan had been so shy in bringing it up to them at first, but here he was: an air of confidence radiating from him that only came when he was in his Sexbang persona. Jack was admittedly a little jealous that Dan held this confidence, but he was also in awe watching it go down.   


“You should watch out, babygirl,” Holly placed her hand on Dan’s chest, “I don’t think you two can handle what I’m into.”

“Try us.” Dan smirked. Holly returned one of her own.

“I like your attitude. Both of you,” Holly snapped her fingers, and Jack and Dan perked up, eyes wide and waiting, “I want everything off but your panties.”

“Yes, sir.” They replied in unison, stripping down to the lace panties that Holly had so graciously picked out for them.

“Good girls,” Holly praised as she walked over to the dresser. Digging around inside, she pulled out a condom, some lube, and a riding crop, holding it tightly in her grasp.

“Are you gonna use that on us?” Jack squeaked out. He shuffled some more in his spot as Holly gave a curt nod, pocketing the condom and lube she’d pulled out.

“Your friend there said you both would be able to take it,” she pointed the crop to Dan, who gulped, “and I’m sure she wouldn’t lie to me.”

“Of course I wouldn’t,” Dan spoke up, “I’m an honest woman, my friend’s just playing shy. She’s a real slut once you get her riled up,  _ right _ ?” Dan nudged Jack, eyebrows knitted together as he waited for Jack to respond.

“Y-yeah,” he said shakily. Dan wasn’t wrong, honestly. Jack was shy when talking about the things that got him sexually excited, but once the act started, he would be begging and moaning like crazy. Even now, as he stood under the eyes of his partners, clad in only panties, he was noticeably hard and bit his lip.

“We’ll have to test that out then,” Holly strided to Jack, shoving him onto the bed, “guess I’ll be having you first.” Holly trailed the leather crop along Jack’s thigh, and he squirmed at the feeling. “You like that, don’t you, princess?” He nodded, face flushed red as Holly’s fingers began teasing at the front of his panties. “Say it.”

“I like it, sir.” Jack whimpered, voice high and breathy.

“Good, good. Now roll over and get on your knees,” Holly demanded. Jack was more than happy to oblige. “And Leigh,” she faced him, “get on the bed and spread your legs in front of him.” Dan scrambled onto the bed, doing as he was told.

“Anything else, sir?” Dan asked obediently.

“Just wait, babygirl,” Holly answered, “lemme just take care of your friend.” Holly groped Jack’s ass, kneading the flesh in her palm as she watched him shake beneath her. His head was tilted up, assumedly to gawk at Dan in front of him. “You know the words to say, right, princess?” He nodded, and Holly nodded as well as she took a step back. She admired the view before her: Jack’s pale ass in the air, his cock visibly straining against the front of the fabric; Dan before him, gasping quietly as he stroked his cock through his panties. It was a beautiful sight, and Holly wanted to drink it all up.

She pulled the crop far behind her before shooting forward, landing a hit on Jack’s left inner thigh. The man let out a yelp, scooting forward.

“You okay?” She broke from her role momentarily to ask. He hummed out an approval and she pulled back again. Hit after hit, Jack took each one well. His skin shone red, and Holly had a feeling he would be feeling this for days, maybe even weeks to come.

Delivering the last smacks, she threw the crop to the ground and grabbed a handful of Jack’s ass. “Such a good girl, taking those hits just like I knew you would,” She used her free hand to reach into her pocket and grabbed the small bottle of lube sitting inside, “now let’s see what else you can take.” Pulling down the zipper of her slacks, she pulled Jack’s panties to the side and ran the pad of her thumb across his asshole, listening to the labored breaths coming from him.

“Fuck,” he whispered.

“Babygirl,” Holly snapped her fingers and Dan’s hand shot off his dick, eyes trained on Holly, “Let princess see your pretty pussy. I think she’d like a taste, isn’t that right?” Jack nodded eagerly and lifted his head. Dan blushed deeply as he pulled his own panties to the side, his cock popping out. Jack’s arms stretched out and he rested his palms on Dan’s thighs. Sticking his tongue out, he flattened it against the underside of Dan’s shaft, slowly licking up to the tip. Dan threw his head back, a long and low moan falling from his lips.

Holly fished her strapon out of her pants, squirting some lube onto her fingers before she brought her index finger to Jack’s hole, circling it before slowly sliding the digit inside. She watched as his grip on Dan’s thighs tightened, as his mouth was too full of cock to make any noises. Holly slowly fingered him, dragging it out for as long as she could while Jack lazily worked his mouth on Dan’s cock. Once she felt that he was prepared, she swiftly pulled her fingers out and pressed the head of her silicone cock against his ass. Jack pushed his hips back desperate to have Holly slid deeper inside him, moaning loudly around Dan’s dick. She gripped Jack’s hips, pulling back and snapping her hips forward harshly, rocking all three of them together slightly.

“Fuck,” Dan gasped, throwing his head back into the pillow when he felt the other man swallow around him and moan, the vibration and tightness of his mouth making his hips buck up as he came into Jack’s mouth. He whimpered helplessly, watching as Holly continued to fuck Jack. Jack’s hands were holding onto Dan’s thighs tightly as his mouth off his cock with a wet pop and pressed his forehead against Dan’s stomach. Dan threaded his fingers through Jack’s hair, petting softly as Holly pounded into him while he moaned wildly into the older man’s belly.

“Harder,” Jack groaned, his breath hot and wet on Dan’s skin. Dan nodded up at Holly, who happily obliged with Jack’s request. The sound of skin slapping flooded the room, Holly reaching around Jack’s hips to take his cock in her hand. She stroked in time with her thrusts, leaning over and biting down on Jack’s shoulder.

“You like when I play with your pussy, princess?” Holly growled. Jack gasped and Dan continued to stroke his hair.

“Shit, shit,  _ shit _ ,” Jack muttered, and before long he was cumming, wet, hot, and sticky all over Holly’s fingers. He pressed his face deeper into Dan’s stomach, body shaking as his orgasm wracked through him.

“Such a good girl,” Holly praised, her thrusts slowing as she pressed open mouthed kisses along his shoulder.

Once she pulled out, Jack collapsed on the bed, crawling up into Dan’s arms and snuggling there. Holly clicked her tongue as she began to undress herself.

“Oh girls?” She sang, pulling her shirt off and letting it fall to the floor, “I hope you didn’t think we were finished here. I’ve given and now,” she dropped her strap harness fall to the floor with a thud, “I deserve to receive.”

 

**Author's Note:**

> My [Tumblr.](https://raptorfics.tumblr.com/) If you liked this, or wanna see something similar to it, come on over!


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